# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Nair Rodriguez-Hornedo' _publ_contact_author_email nrh@umich.edu loop_ _publ_author_name C.Maheshwari V.Andre S.Lingireddy L.Roy M.Duarte N.Rodriguez-Hornedo data_GBPL4ABA _database_code_depnum_ccdc_archive 'CCDC 856629' #TrackingRef '- GBPL4ABA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common GBPL4ABA _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 N2 O3' _chemical_formula_sum 'C16 H22 N2 O3' _chemical_formula_weight 290.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.9280(6) _cell_length_b 18.465(2) _cell_length_c 14.208(1) _cell_angle_alpha 90.00 _cell_angle_beta 99.259(5) _cell_angle_gamma 90.00 _cell_volume 1535.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2218 _cell_measurement_theta_min 1.82 _cell_measurement_theta_max 25.70 _exptl_crystal_description parallelipipedic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10262 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.70 _reflns_number_total 2922 _reflns_number_gt 2218 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER APEX2 (Bruker, 2005)' _computing_cell_refinement 'BRUKER SMART (Bruker, 2005)' _computing_data_reduction 'BRUKER SAINT (Bruker, 2005)' _computing_structure_solution 'SIR 97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0856P)^2^+0.1269P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2922 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1539 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7892(2) 0.56887(7) 1.01128(10) 0.0317(4) Uani 1 1 d . . . N1 N 0.7864(3) 0.50402(9) 0.87468(12) 0.0258(4) Uani 1 1 d . . . C1 C 0.7028(3) 0.55242(10) 0.92792(14) 0.0247(5) Uani 1 1 d . . . C2 C 0.4872(3) 0.58312(10) 0.87216(15) 0.0272(5) Uani 1 1 d . . . H2A H 0.4855 0.6355 0.8774 0.033 Uiso 1 1 calc R . . H2B H 0.3539 0.5638 0.8951 0.033 Uiso 1 1 calc R . . C3 C 0.4899(3) 0.55981(10) 0.76855(14) 0.0224(5) Uani 1 1 d . . . C4 C 0.6505(3) 0.49327(10) 0.78088(13) 0.0228(4) Uani 1 1 d . . . H4A H 0.5638 0.4486 0.7786 0.027 Uiso 1 1 calc R . . H4B H 0.7466 0.4921 0.7317 0.027 Uiso 1 1 calc R . . C5 C 0.2517(3) 0.54041(13) 0.71731(15) 0.0352(5) Uani 1 1 d . . . H5A H 0.1921 0.5007 0.7506 0.042 Uiso 1 1 calc R . . H5B H 0.1514 0.5817 0.7193 0.042 Uiso 1 1 calc R . . C6 C 0.2505(4) 0.51880(15) 0.61429(17) 0.0479(7) Uani 1 1 d . . . H6A H 0.3415 0.4754 0.6118 0.058 Uiso 1 1 calc R . . H6B H 0.0953 0.5082 0.5841 0.058 Uiso 1 1 calc R . . C7 C 0.3469(5) 0.57945(16) 0.56126(18) 0.0597(9) Uani 1 1 d . . . H7A H 0.2468 0.6212 0.5587 0.072 Uiso 1 1 calc R . . H7B H 0.3517 0.5641 0.4963 0.072 Uiso 1 1 calc R . . C8 C 0.5869(5) 0.60104(13) 0.60891(17) 0.0479(7) Uani 1 1 d . . . H8A H 0.6917 0.5615 0.6035 0.058 Uiso 1 1 calc R . . H8B H 0.6372 0.6427 0.5762 0.058 Uiso 1 1 calc R . . C9 C 0.5928(4) 0.61938(11) 0.71371(16) 0.0347(5) Uani 1 1 d . . . H9A H 0.5091 0.6640 0.7184 0.042 Uiso 1 1 calc R . . H9B H 0.7500 0.6275 0.7432 0.042 Uiso 1 1 calc R . . O2 O 0.5028(2) 0.87550(7) 0.70756(10) 0.0295(4) Uani 1 1 d . . . O3 O 0.1481(2) 0.84677(7) 0.63916(10) 0.0292(4) Uani 1 1 d . . . H04 H 0.1851 0.8703 0.5951 0.044 Uiso 1 1 calc R . . N2 N 0.1657(4) 0.69687(10) 1.04204(14) 0.0335(5) Uani 1 1 d . . . C10 C 0.3219(3) 0.84579(9) 0.71242(14) 0.0216(4) Uani 1 1 d . . . C11 C 0.2735(3) 0.80688(9) 0.79704(13) 0.0207(4) Uani 1 1 d . . . C12 C 0.0652(3) 0.77272(11) 0.80159(14) 0.0271(5) Uani 1 1 d . . . H12 H -0.0512 0.7746 0.7493 0.032 Uiso 1 1 calc R . . C13 C 0.0303(3) 0.73645(11) 0.88224(15) 0.0281(5) Uani 1 1 d . . . H13 H -0.1094 0.7140 0.8837 0.034 Uiso 1 1 calc R . . C14 C 0.2011(3) 0.73275(10) 0.96209(14) 0.0224(4) Uani 1 1 d . . . C15 C 0.4088(3) 0.76855(10) 0.95804(14) 0.0248(5) Uani 1 1 d . . . H15 H 0.5242 0.7678 1.0108 0.030 Uiso 1 1 calc R . . C16 C 0.4425(3) 0.80441(9) 0.87734(14) 0.0225(4) Uani 1 1 d . . . H16 H 0.5812 0.8276 0.8760 0.027 Uiso 1 1 calc R . . H01 H 0.894(4) 0.4788(13) 0.8941(17) 0.038(7) Uiso 1 1 d . . . H02 H 0.280(5) 0.6920(13) 1.0827(18) 0.047(8) Uiso 1 1 d . . . H03 H 0.048(4) 0.6703(12) 1.0364(17) 0.038(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0352(8) 0.0386(8) 0.0195(8) -0.0068(6) -0.0010(6) 0.0035(6) N1 0.0256(9) 0.0285(9) 0.0218(9) -0.0012(7) -0.0008(8) 0.0077(7) C1 0.0271(10) 0.0245(10) 0.0224(11) -0.0027(8) 0.0042(9) -0.0027(8) C2 0.0250(10) 0.0297(10) 0.0267(11) -0.0064(9) 0.0040(9) 0.0028(8) C3 0.0215(9) 0.0239(10) 0.0215(10) -0.0032(8) 0.0021(8) 0.0023(7) C4 0.0244(10) 0.0233(10) 0.0201(10) -0.0024(8) 0.0012(8) 0.0010(8) C5 0.0228(10) 0.0463(13) 0.0346(13) -0.0099(11) -0.0017(9) 0.0059(9) C6 0.0340(12) 0.0680(17) 0.0366(14) -0.0193(13) -0.0102(11) 0.0117(12) C7 0.073(2) 0.0752(19) 0.0258(13) -0.0027(13) -0.0065(13) 0.0439(16) C8 0.0766(18) 0.0358(12) 0.0366(14) 0.0125(11) 0.0250(13) 0.0118(12) C9 0.0449(13) 0.0222(10) 0.0382(13) 0.0020(9) 0.0104(11) 0.0029(9) O2 0.0286(8) 0.0334(8) 0.0264(8) 0.0025(6) 0.0047(6) -0.0086(6) O3 0.0279(7) 0.0391(9) 0.0198(7) 0.0050(6) 0.0013(6) -0.0052(6) N2 0.0311(11) 0.0404(11) 0.0280(11) 0.0092(9) 0.0017(9) -0.0059(9) C10 0.0230(10) 0.0198(9) 0.0217(10) -0.0052(8) 0.0029(8) 0.0015(7) C11 0.0231(9) 0.0189(9) 0.0203(10) -0.0024(8) 0.0039(8) 0.0009(7) C12 0.0210(10) 0.0330(11) 0.0253(11) 0.0025(9) -0.0020(8) -0.0031(8) C13 0.0204(10) 0.0328(11) 0.0312(12) 0.0044(9) 0.0039(9) -0.0053(8) C14 0.0261(10) 0.0202(9) 0.0217(10) -0.0017(8) 0.0058(8) 0.0010(8) C15 0.0255(10) 0.0243(10) 0.0223(10) -0.0022(8) -0.0033(8) -0.0022(8) C16 0.0207(9) 0.0209(9) 0.0257(11) -0.0036(8) 0.0032(8) -0.0021(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.250(2) . ? N1 C1 1.318(3) . ? N1 C4 1.456(2) . ? C1 C2 1.502(3) . ? C2 C3 1.536(3) . ? C3 C5 1.523(3) . ? C3 C9 1.530(3) . ? C3 C4 1.547(3) . ? C5 C6 1.516(3) . ? C6 C7 1.512(4) . ? C7 C8 1.527(4) . ? C8 C9 1.522(3) . ? O2 C10 1.216(2) . ? O3 C10 1.341(2) . ? N2 C14 1.360(3) . ? C10 C11 1.468(3) . ? C11 C16 1.393(3) . ? C11 C12 1.397(3) . ? C12 C13 1.371(3) . ? C13 C14 1.395(3) . ? C14 C15 1.407(3) . ? C15 C16 1.366(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 114.46(17) . . ? O1 C1 N1 125.04(18) . . ? O1 C1 C2 126.31(18) . . ? N1 C1 C2 108.65(17) . . ? C1 C2 C3 105.09(16) . . ? C5 C3 C9 109.89(17) . . ? C5 C3 C2 111.85(17) . . ? C9 C3 C2 110.68(16) . . ? C5 C3 C4 111.92(16) . . ? C9 C3 C4 109.88(16) . . ? C2 C3 C4 102.42(15) . . ? N1 C4 C3 103.61(15) . . ? C6 C5 C3 112.57(18) . . ? C7 C6 C5 110.0(2) . . ? C6 C7 C8 111.85(19) . . ? C9 C8 C7 111.4(2) . . ? C8 C9 C3 112.96(18) . . ? O2 C10 O3 121.58(18) . . ? O2 C10 C11 123.88(17) . . ? O3 C10 C11 114.54(16) . . ? C16 C11 C12 118.16(18) . . ? C16 C11 C10 118.52(16) . . ? C12 C11 C10 123.32(17) . . ? C13 C12 C11 120.82(17) . . ? C12 C13 C14 121.06(18) . . ? N2 C14 C13 120.91(18) . . ? N2 C14 C15 121.11(18) . . ? C13 C14 C15 117.97(18) . . ? C16 C15 C14 120.61(17) . . ? C15 C16 C11 121.34(17) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.70 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.365 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.077 # Attachment '- GBPLGA.cif' data_GBPLGA _database_code_depnum_ccdc_archive 'CCDC 856632' #TrackingRef '- GBPLGA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common GBPLGA _chemical_melting_point ? _chemical_formula_moiety 'C9 H15 N O, C7 H6 O4' _chemical_formula_sum 'C16 H21 N O5' _chemical_formula_weight 307.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.9663(6) _cell_length_b 27.045(3) _cell_length_c 9.4703(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.008(2) _cell_angle_gamma 90.00 _cell_volume 1461.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 7157 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 23.08 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9597 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2007/4) Bruker AXS area detector absorption and other corrections, University of Gottingen, Germany 2007. ; _exptl_special_details ; 2490 frames x 25 sec. @ 5.055 cm; 0.5 deg steps in omega, 0.45 in phi ; _diffrn_ambient_temperature 85(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32048 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 28.37 _reflns_number_total 3647 _reflns_number_gt 3077 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART-APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.7235P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3647 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.3174(2) 0.09003(5) 0.66363(13) 0.0189(3) Uani 1 1 d . . . H1 H 1.317(3) 0.0617(8) 0.711(2) 0.033(5) Uiso 1 1 d . . . O1 O 0.95236(17) 0.08109(4) 0.49945(11) 0.0204(2) Uani 1 1 d . . . O2 O -0.15015(17) -0.00311(4) 0.20735(11) 0.0202(2) Uani 1 1 d . . . O3 O 0.20161(18) -0.00820(4) 0.37598(11) 0.0211(2) Uani 1 1 d . . . H3 H 0.124(4) -0.0331(8) 0.412(2) 0.039(6) Uiso 1 1 d . . . O4 O -0.20027(18) 0.05560(4) -0.02032(11) 0.0206(2) Uani 1 1 d . . . H4 H -0.237(4) 0.0322(10) 0.036(3) 0.057(7) Uiso 1 1 d . . . O5 O 0.69772(17) 0.12281(4) 0.24605(11) 0.0207(2) Uani 1 1 d . . . H5 H 0.773(4) 0.1057(8) 0.328(3) 0.043(6) Uiso 1 1 d . . . C1 C 1.1423(2) 0.10366(5) 0.54889(14) 0.0165(3) Uani 1 1 d . . . C2 C 1.2070(2) 0.15100(5) 0.48650(14) 0.0167(3) Uani 1 1 d . . . H2A H 1.0740 0.1745 0.4618 0.020 Uiso 1 1 calc R . . H2B H 1.2555 0.1445 0.3968 0.020 Uiso 1 1 calc R . . C3 C 1.4134(2) 0.17122(5) 0.61238(14) 0.0154(3) Uani 1 1 d . . . C4 C 1.5178(2) 0.12330(5) 0.69349(15) 0.0183(3) Uani 1 1 d . . . H4B H 1.6416 0.1098 0.6540 0.022 Uiso 1 1 calc R . . H4C H 1.5846 0.1292 0.8008 0.022 Uiso 1 1 calc R . . C5 C 1.5935(2) 0.19980(5) 0.55854(15) 0.0179(3) Uani 1 1 d . . . H5B H 1.7338 0.2061 0.6432 0.021 Uiso 1 1 calc R . . H5C H 1.6423 0.1793 0.4860 0.021 Uiso 1 1 calc R . . C6 C 1.4978(2) 0.24905(6) 0.48703(15) 0.0190(3) Uani 1 1 d . . . H6A H 1.6235 0.2670 0.4596 0.023 Uiso 1 1 calc R . . H6B H 1.3691 0.2427 0.3955 0.023 Uiso 1 1 calc R . . C7 C 1.4064(3) 0.28117(5) 0.59074(15) 0.0198(3) Uani 1 1 d . . . H7A H 1.5389 0.2911 0.6765 0.024 Uiso 1 1 calc R . . H7B H 1.3353 0.3116 0.5383 0.024 Uiso 1 1 calc R . . C8 C 1.2244(2) 0.25360(5) 0.64500(15) 0.0192(3) Uani 1 1 d . . . H8A H 1.0828 0.2477 0.5609 0.023 Uiso 1 1 calc R . . H8B H 1.1786 0.2742 0.7185 0.023 Uiso 1 1 calc R . . C9 C 1.3206(2) 0.20428(5) 0.71496(14) 0.0168(3) Uani 1 1 d . . . H9A H 1.1950 0.1864 0.7428 0.020 Uiso 1 1 calc R . . H9B H 1.4491 0.2107 0.8065 0.020 Uiso 1 1 calc R . . C10 C 0.0550(2) 0.01069(5) 0.25555(15) 0.0175(3) Uani 1 1 d . . . C11 C 0.1557(2) 0.04972(5) 0.18516(14) 0.0163(3) Uani 1 1 d . . . C12 C 0.0219(2) 0.07030(5) 0.05089(15) 0.0169(3) Uani 1 1 d . . . C13 C 0.1200(2) 0.10721(5) -0.01443(15) 0.0186(3) Uani 1 1 d . . . H13A H 0.0318 0.1209 -0.1062 0.022 Uiso 1 1 calc R . . C14 C 0.3439(2) 0.12407(5) 0.05252(15) 0.0185(3) Uani 1 1 d . . . H14A H 0.4073 0.1497 0.0074 0.022 Uiso 1 1 calc R . . C15 C 0.4786(2) 0.10379(5) 0.18624(15) 0.0170(3) Uani 1 1 d . . . C16 C 0.3853(2) 0.06641(5) 0.25070(14) 0.0168(3) Uani 1 1 d . . . H16A H 0.4773 0.0519 0.3402 0.020 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0195(6) 0.0199(6) 0.0153(5) 0.0033(5) 0.0021(4) 0.0001(5) O1 0.0196(5) 0.0233(5) 0.0159(5) 0.0025(4) 0.0017(4) -0.0043(4) O2 0.0185(5) 0.0228(5) 0.0182(5) 0.0018(4) 0.0040(4) -0.0014(4) O3 0.0205(5) 0.0236(6) 0.0165(5) 0.0065(4) 0.0014(4) -0.0026(4) O4 0.0178(5) 0.0249(6) 0.0163(5) 0.0023(4) 0.0007(4) -0.0015(4) O5 0.0181(5) 0.0253(6) 0.0167(5) 0.0039(4) 0.0016(4) -0.0037(4) C1 0.0182(6) 0.0205(7) 0.0113(6) -0.0009(5) 0.0050(5) -0.0003(5) C2 0.0176(6) 0.0208(7) 0.0107(6) 0.0002(5) 0.0025(5) -0.0009(5) C3 0.0148(6) 0.0199(7) 0.0107(6) 0.0000(5) 0.0026(5) -0.0003(5) C4 0.0159(6) 0.0212(7) 0.0159(6) 0.0011(5) 0.0016(5) 0.0003(5) C5 0.0159(6) 0.0230(7) 0.0151(6) -0.0006(5) 0.0051(5) -0.0008(5) C6 0.0200(7) 0.0239(7) 0.0140(6) 0.0014(5) 0.0063(5) -0.0030(5) C7 0.0231(7) 0.0201(7) 0.0166(6) 0.0017(5) 0.0064(5) -0.0007(6) C8 0.0212(7) 0.0206(7) 0.0178(6) 0.0004(5) 0.0087(5) 0.0012(5) C9 0.0186(6) 0.0216(7) 0.0104(6) 0.0004(5) 0.0048(5) -0.0005(5) C10 0.0191(7) 0.0183(7) 0.0145(6) -0.0009(5) 0.0037(5) 0.0017(5) C11 0.0192(7) 0.0174(7) 0.0131(6) -0.0003(5) 0.0059(5) 0.0018(5) C12 0.0164(6) 0.0195(7) 0.0137(6) -0.0016(5) 0.0028(5) 0.0018(5) C13 0.0204(7) 0.0219(7) 0.0126(6) 0.0023(5) 0.0036(5) 0.0028(5) C14 0.0208(7) 0.0201(7) 0.0153(6) 0.0021(5) 0.0065(5) 0.0006(5) C15 0.0170(6) 0.0203(7) 0.0136(6) -0.0014(5) 0.0043(5) -0.0004(5) C16 0.0190(7) 0.0185(7) 0.0120(6) 0.0006(5) 0.0032(5) 0.0015(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3206(17) . ? N1 C4 1.4566(18) . ? O1 C1 1.2512(17) . ? O2 C10 1.2326(17) . ? O3 C10 1.3202(16) . ? O4 C12 1.3591(17) . ? O5 C15 1.3643(16) . ? C1 C2 1.507(2) . ? C2 C3 1.5419(18) . ? C3 C5 1.5272(19) . ? C3 C9 1.5375(19) . ? C3 C4 1.5420(19) . ? C5 C6 1.527(2) . ? C6 C7 1.526(2) . ? C7 C8 1.525(2) . ? C8 C9 1.525(2) . ? C10 C11 1.468(2) . ? C11 C16 1.4029(19) . ? C11 C12 1.4038(18) . ? C12 C13 1.391(2) . ? C13 C14 1.378(2) . ? C14 C15 1.3982(19) . ? C15 C16 1.380(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 113.22(12) . . ? O1 C1 N1 125.71(13) . . ? O1 C1 C2 125.15(12) . . ? N1 C1 C2 109.14(12) . . ? C1 C2 C3 103.68(10) . . ? C5 C3 C9 109.57(11) . . ? C5 C3 C2 113.70(11) . . ? C9 C3 C2 109.95(11) . . ? C5 C3 C4 111.74(11) . . ? C9 C3 C4 109.98(11) . . ? C2 C3 C4 101.65(11) . . ? N1 C4 C3 103.50(11) . . ? C6 C5 C3 112.41(11) . . ? C7 C6 C5 111.62(11) . . ? C8 C7 C6 111.23(12) . . ? C7 C8 C9 111.08(12) . . ? C8 C9 C3 113.16(11) . . ? O2 C10 O3 122.55(13) . . ? O2 C10 C11 122.93(12) . . ? O3 C10 C11 114.52(12) . . ? C16 C11 C12 119.75(13) . . ? C16 C11 C10 120.46(12) . . ? C12 C11 C10 119.79(12) . . ? O4 C12 C13 117.76(12) . . ? O4 C12 C11 123.18(13) . . ? C13 C12 C11 119.06(13) . . ? C14 C13 C12 120.69(12) . . ? C13 C14 C15 120.67(13) . . ? O5 C15 C16 123.66(12) . . ? O5 C15 C14 117.09(12) . . ? C16 C15 C14 119.26(13) . . ? C15 C16 C11 120.54(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.89(2) 2.13(2) 2.9544(16) 153.5(17) 3_656 O3 H3 O1 0.94(2) 1.68(2) 2.5990(15) 166.9(19) 3_656 O5 H5 O1 0.90(2) 1.79(2) 2.6847(14) 170(2) . O4 H4 O2 0.89(3) 1.82(3) 2.6233(15) 148(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.355 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.048 # Attachment '- GBPL4HBA.cif' data_GBPL4HBA _database_code_depnum_ccdc_archive 'CCDC 871254' #TrackingRef '- GBPL4HBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common GBPL4HBA _chemical_melting_point ? _chemical_formula_moiety 'C16 H21 N O4' _chemical_formula_sum 'C16 H21 N O4' _chemical_formula_weight 291.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3900(4) _cell_length_b 10.0780(7) _cell_length_c 12.2260(8) _cell_angle_alpha 81.714(3) _cell_angle_beta 82.039(3) _cell_angle_gamma 76.597(3) _cell_volume 753.37(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3034 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 26.42 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8801 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 26.42 _reflns_number_total 3034 _reflns_number_gt 2182 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER APEX2 (Bruker, 2005)' _computing_cell_refinement 'BRUKER SMART (Bruker, 2005)' _computing_data_reduction 'BRUKER SAINT (Bruker, 2005)' _computing_structure_solution 'SIR 97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.2071P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3034 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1300 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3223(2) 0.53900(14) 0.12859(11) 0.0477(4) Uani 1 1 d . . . N1 N 0.6652(3) 0.40822(17) 0.11275(17) 0.0516(5) Uani 1 1 d . . . C1 C 0.4931(3) 0.47824(18) 0.16854(16) 0.0411(4) Uani 1 1 d . . . C2 C 0.5396(4) 0.4721(2) 0.28608(17) 0.0567(6) Uani 1 1 d . A . H2A H 0.4199 0.4503 0.3381 0.068 Uiso 1 1 calc R . . H2B H 0.5660 0.5589 0.3000 0.068 Uiso 1 1 calc R . . C3 C 0.7436(5) 0.3571(2) 0.2964(2) 0.0786(9) Uani 1 1 d . . . C4 C 0.8485(4) 0.3538(2) 0.1751(2) 0.0713(8) Uani 1 1 d . A . H4A H 0.9544 0.4110 0.1583 0.086 Uiso 1 1 calc R . . H4B H 0.9174 0.2608 0.1602 0.086 Uiso 1 1 calc R . . C5 C 0.7098(7) 0.2115(4) 0.3239(4) 0.0458(10) Uani 0.612(5) 1 d P A 2 H5A H 0.8442 0.1458 0.3080 0.055 Uiso 0.612(5) 1 calc PR A 2 H5B H 0.6026 0.1968 0.2806 0.055 Uiso 0.612(5) 1 calc PR A 2 C6 C 0.6312(9) 0.1956(5) 0.4480(4) 0.0652(15) Uani 0.612(5) 1 d P A 2 H6A H 0.6060 0.1038 0.4702 0.078 Uiso 0.612(5) 1 calc PR A 2 H6B H 0.4952 0.2606 0.4620 0.078 Uiso 0.612(5) 1 calc PR A 2 C7 C 0.7977(10) 0.2206(6) 0.5173(3) 0.0678(15) Uani 0.612(5) 1 d P A 2 H7A H 0.7410 0.2149 0.5952 0.081 Uiso 0.612(5) 1 calc PR A 2 H7B H 0.9292 0.1502 0.5090 0.081 Uiso 0.612(5) 1 calc PR A 2 C8 C 0.8491(7) 0.3609(4) 0.4802(3) 0.0536(12) Uani 0.612(5) 1 d P A 2 H8A H 0.9587 0.3734 0.5229 0.064 Uiso 0.612(5) 1 calc PR A 2 H8B H 0.7201 0.4315 0.4944 0.064 Uiso 0.612(5) 1 calc PR A 2 C9 C 0.9302(7) 0.3760(4) 0.3567(3) 0.0378(9) Uani 0.612(5) 1 d P A 2 H9A H 1.0601 0.3066 0.3408 0.045 Uiso 0.612(5) 1 calc PR A 2 H9B H 0.9622 0.4660 0.3335 0.045 Uiso 0.612(5) 1 calc PR A 2 C5A C 0.6166(12) 0.2367(6) 0.3806(7) 0.0459(15) Uani 0.388(5) 1 d P A 1 H5A1 H 0.5311 0.2766 0.4445 0.055 Uiso 0.388(5) 1 calc PR A 1 H5A2 H 0.5222 0.2052 0.3391 0.055 Uiso 0.388(5) 1 calc PR A 1 C6A C 0.7966(13) 0.1193(6) 0.4170(5) 0.059(2) Uani 0.388(5) 1 d P A 1 H6A1 H 0.8885 0.0865 0.3521 0.071 Uiso 0.388(5) 1 calc PR A 1 H6A2 H 0.7353 0.0443 0.4567 0.071 Uiso 0.388(5) 1 calc PR A 1 C7A C 0.9324(15) 0.1650(6) 0.4923(6) 0.059(2) Uani 0.388(5) 1 d P A 1 H7A1 H 0.8453 0.1864 0.5617 0.071 Uiso 0.388(5) 1 calc PR A 1 H7A2 H 1.0544 0.0907 0.5094 0.071 Uiso 0.388(5) 1 calc PR A 1 C8A C 1.0142(9) 0.2906(5) 0.4357(4) 0.0455(16) Uani 0.388(5) 1 d P A 1 H8A1 H 1.0939 0.3204 0.4862 0.055 Uiso 0.388(5) 1 calc PR A 1 H8A2 H 1.1130 0.2660 0.3705 0.055 Uiso 0.388(5) 1 calc PR A 1 C9A C 0.8328(10) 0.4070(6) 0.4016(5) 0.0348(13) Uani 0.388(5) 1 d P A 1 H9A1 H 0.8847 0.4909 0.3783 0.042 Uiso 0.388(5) 1 calc PR A 1 H9A2 H 0.7188 0.4226 0.4626 0.042 Uiso 0.388(5) 1 calc PR A 1 H01 H 0.670(3) 0.406(2) 0.0397(17) 0.042 Uiso 1 1 d . . . O2 O 1.0438(2) 0.71159(13) 0.25149(11) 0.0437(3) Uani 1 1 d . . . H02 H 1.1282 0.6600 0.2114 0.066 Uiso 1 1 calc R . . C10 C 0.8574(3) 0.76022(17) 0.20516(14) 0.0345(4) Uani 1 1 d . . . C11 C 0.6928(3) 0.85028(18) 0.26163(14) 0.0376(4) Uani 1 1 d . . . H11 H 0.7138 0.8749 0.3291 0.045 Uiso 1 1 calc R . . C12 C 0.4992(3) 0.90282(17) 0.21782(14) 0.0359(4) Uani 1 1 d . . . H12 H 0.3905 0.9633 0.2558 0.043 Uiso 1 1 calc R . . C13 C 0.4645(3) 0.86628(16) 0.11707(14) 0.0313(4) Uani 1 1 d . . . C14 C 0.6292(3) 0.77614(17) 0.06149(14) 0.0344(4) Uani 1 1 d . . . H14 H 0.6080 0.7510 -0.0057 0.041 Uiso 1 1 calc R . . C15 C 0.8232(3) 0.72367(18) 0.10458(15) 0.0369(4) Uani 1 1 d . . . H15 H 0.9320 0.6635 0.0664 0.044 Uiso 1 1 calc R . . C16 C 0.2594(3) 0.92162(16) 0.06848(14) 0.0331(4) Uani 1 1 d . . . O3 O 0.1176(2) 1.01186(12) 0.12093(10) 0.0391(3) Uani 1 1 d . . . H03 H 0.0093 1.0364 0.0879 0.047 Uiso 0.66(3) 1 calc PR B 4 O4 O 0.2280(2) 0.88227(12) -0.01872(10) 0.0404(3) Uani 1 1 d . . . H04 H 0.1132 0.9275 -0.0393 0.048 Uiso 0.34(3) 1 calc PR B 3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0360(8) 0.0478(8) 0.0608(9) -0.0164(6) -0.0114(6) -0.0019(6) N1 0.0430(10) 0.0464(9) 0.0707(12) -0.0310(9) -0.0261(9) 0.0062(8) C1 0.0454(12) 0.0319(9) 0.0515(11) -0.0128(8) -0.0144(9) -0.0095(8) C2 0.0810(16) 0.0494(12) 0.0527(12) -0.0090(10) -0.0193(11) -0.0317(12) C3 0.104(2) 0.0376(12) 0.116(2) 0.0172(13) -0.0796(18) -0.0343(13) C4 0.0680(16) 0.0419(12) 0.113(2) -0.0276(12) -0.0579(15) 0.0090(11) C5 0.064(3) 0.0413(19) 0.041(2) -0.0072(16) -0.0108(19) -0.0262(18) C6 0.108(4) 0.062(3) 0.042(2) 0.005(2) -0.007(2) -0.058(3) C7 0.115(5) 0.070(3) 0.034(2) 0.003(2) -0.008(2) -0.057(3) C8 0.075(3) 0.066(2) 0.032(2) -0.0088(18) -0.0062(18) -0.038(2) C9 0.050(2) 0.0381(18) 0.0303(19) -0.0061(14) -0.0078(17) -0.0163(17) C5A 0.063(4) 0.045(3) 0.041(4) -0.011(3) -0.008(3) -0.029(3) C6A 0.090(5) 0.039(3) 0.061(4) 0.000(3) -0.033(4) -0.028(3) C7A 0.099(6) 0.040(3) 0.047(4) -0.003(3) -0.034(4) -0.018(4) C8A 0.049(3) 0.050(3) 0.045(3) -0.009(2) -0.019(3) -0.016(3) C9A 0.041(3) 0.037(3) 0.032(3) -0.010(2) -0.002(2) -0.017(2) O2 0.0349(7) 0.0452(7) 0.0517(8) -0.0123(6) -0.0123(6) -0.0015(6) C10 0.0289(9) 0.0328(9) 0.0435(10) -0.0040(7) -0.0069(8) -0.0083(7) C11 0.0400(10) 0.0379(10) 0.0380(9) -0.0098(7) -0.0074(8) -0.0098(8) C12 0.0341(10) 0.0317(9) 0.0422(10) -0.0110(7) -0.0021(8) -0.0052(7) C13 0.0293(9) 0.0270(8) 0.0392(9) -0.0048(7) -0.0034(7) -0.0090(7) C14 0.0348(10) 0.0341(9) 0.0372(9) -0.0104(7) -0.0025(7) -0.0102(7) C15 0.0317(10) 0.0351(9) 0.0446(10) -0.0122(8) -0.0019(8) -0.0049(7) C16 0.0319(10) 0.0262(8) 0.0429(10) -0.0062(7) -0.0028(8) -0.0091(7) O3 0.0337(7) 0.0333(6) 0.0497(7) -0.0110(5) -0.0073(6) -0.0008(5) O4 0.0353(7) 0.0380(7) 0.0511(8) -0.0146(6) -0.0128(6) -0.0040(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.248(2) . ? N1 C1 1.320(3) . ? N1 C4 1.443(3) . ? C1 C2 1.497(3) . ? C2 C3 1.537(4) . ? C3 C5 1.516(4) . ? C3 C4 1.542(4) . ? C3 C9 1.546(4) . ? C3 C9A 1.659(6) . ? C3 C5A 1.748(7) . ? C5 C6 1.528(6) . ? C6 C7 1.533(6) . ? C7 C8 1.517(5) . ? C8 C9 1.525(5) . ? C5A C6A 1.510(10) . ? C6A C7A 1.530(8) . ? C7A C8A 1.520(9) . ? C8A C9A 1.502(8) . ? O2 C10 1.347(2) . ? C10 C15 1.392(2) . ? C10 C11 1.394(2) . ? C11 C12 1.377(2) . ? C12 C13 1.395(2) . ? C13 C14 1.390(2) . ? C13 C16 1.471(2) . ? C14 C15 1.375(3) . ? C16 O4 1.246(2) . ? C16 O3 1.298(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 114.98(19) . . ? O1 C1 N1 125.06(18) . . ? O1 C1 C2 126.55(18) . . ? N1 C1 C2 108.39(18) . . ? C1 C2 C3 104.23(19) . . ? C5 C3 C2 116.8(3) . . ? C5 C3 C4 100.6(3) . . ? C2 C3 C4 102.82(18) . . ? C5 C3 C9 110.4(2) . . ? C2 C3 C9 120.3(2) . . ? C4 C3 C9 102.1(3) . . ? C5 C3 C9A 111.2(3) . . ? C2 C3 C9A 98.1(3) . . ? C4 C3 C9A 128.1(3) . . ? C9 C3 C9A 28.89(19) . . ? C5 C3 C5A 30.0(2) . . ? C2 C3 C5A 96.6(3) . . ? C4 C3 C5A 128.9(3) . . ? C9 C3 C5A 107.8(3) . . ? C9A C3 C5A 94.3(3) . . ? N1 C4 C3 102.4(2) . . ? C3 C5 C6 105.9(3) . . ? C5 C6 C7 111.1(4) . . ? C8 C7 C6 110.6(4) . . ? C7 C8 C9 111.1(3) . . ? C8 C9 C3 105.3(3) . . ? C6A C5A C3 105.8(5) . . ? C5A C6A C7A 110.8(5) . . ? C8A C7A C6A 110.5(5) . . ? C9A C8A C7A 112.1(5) . . ? C8A C9A C3 104.9(4) . . ? O2 C10 C15 122.81(15) . . ? O2 C10 C11 117.92(15) . . ? C15 C10 C11 119.27(16) . . ? C12 C11 C10 120.18(16) . . ? C11 C12 C13 120.65(16) . . ? C14 C13 C12 118.79(16) . . ? C14 C13 C16 119.64(15) . . ? C12 C13 C16 121.58(15) . . ? C15 C14 C13 120.86(16) . . ? C14 C15 C10 120.25(16) . . ? O4 C16 O3 123.05(16) . . ? O4 C16 C13 120.44(15) . . ? O3 C16 C13 116.51(15) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.345 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.038 # Attachment '- GBPLFA.cif' data_GBPLFA _database_code_depnum_ccdc_archive 'CCDC 871255' #TrackingRef '- GBPLFA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common GBPLFA _chemical_melting_point ? _chemical_formula_moiety 'C9 H15 N O, 0.5(C4 H6 O4)' _chemical_formula_sum 'C11 H18 N O3' _chemical_formula_weight 212.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7040(3) _cell_length_b 6.0110(4) _cell_length_c 17.802(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.372(3) _cell_angle_gamma 90.00 _cell_volume 1122.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2097 _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 25.64 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7576 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.64 _reflns_number_total 2097 _reflns_number_gt 1310 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER APEX2 (Bruker, 2005)' _computing_cell_refinement 'BRUKER SMART (Bruker, 2005)' _computing_data_reduction 'BRUKER SAINT (Bruker, 2005)' _computing_structure_solution 'SIR 97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1148P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2097 _refine_ls_number_parameters 144 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1068 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.2063 _refine_ls_wR_factor_gt 0.1771 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.0288(3) 0.0354(5) 0.62769(18) 0.0418(8) Uani 1 1 d . . . H2A H 0.0177 -0.1105 0.6040 0.050 Uiso 1 1 calc R A 1 H2B H -0.0374 0.0587 0.6571 0.050 Uiso 1 1 calc R A 1 C3 C 0.1616(3) 0.0576(4) 0.67890(16) 0.0303(7) Uani 1 1 d . C . C4 C 0.2343(3) 0.2038(5) 0.63045(17) 0.0350(7) Uani 1 1 d . . . H4A H 0.2904 0.3065 0.6630 0.042 Uiso 1 1 calc R B 1 H4B H 0.2852 0.1118 0.6033 0.042 Uiso 1 1 calc R B 1 C5 C 0.2253(3) -0.1684(4) 0.6970(2) 0.0471(9) Uani 1 1 d . . . H5A H 0.1694 -0.2643 0.7193 0.057 Uiso 1 1 calc R C . H5B H 0.2384 -0.2368 0.6498 0.057 Uiso 1 1 calc R . . C6 C 0.3530(3) -0.1485(5) 0.7524(3) 0.0614(11) Uani 1 1 d . C . H6A H 0.3884 -0.2957 0.7644 0.074 Uiso 1 1 calc R . . H6B H 0.4119 -0.0651 0.7282 0.074 Uiso 1 1 calc R . . C7 C 0.3381(3) -0.0324(6) 0.8258(2) 0.0637(11) Uani 1 1 d . . . H7A H 0.2853 -0.1225 0.8523 0.076 Uiso 1 1 calc R C . H7B H 0.4210 -0.0165 0.8591 0.076 Uiso 1 1 calc R . . C8 C 0.2782(3) 0.1943(6) 0.8093(2) 0.0544(9) Uani 1 1 d . C . H8A H 0.3354 0.2901 0.7881 0.065 Uiso 1 1 calc R . . H8B H 0.2642 0.2607 0.8566 0.065 Uiso 1 1 calc R . . C9 C 0.1517(3) 0.1757(5) 0.75283(17) 0.0381(7) Uani 1 1 d . . . H9A H 0.0916 0.0960 0.7772 0.046 Uiso 1 1 calc R C . H9B H 0.1180 0.3240 0.7407 0.046 Uiso 1 1 calc R . . O1 O -0.0688(5) 0.2815(9) 0.5253(4) 0.044(2) Uani 0.360(6) 1 d P C 2 C1 C 0.0087(12) 0.246(2) 0.5794(7) 0.035(3) Uiso 0.360(6) 1 d P C 2 N1 N 0.1291(10) 0.2958(18) 0.5687(6) 0.020(3) Uiso 0.360(6) 1 d PD C 2 H01 H 0.1435 0.3723 0.5304 0.024 Uiso 0.360(6) 1 calc PRD C 2 O1A O 0.1470(3) 0.4483(5) 0.5242(2) 0.0480(12) Uani 0.640(6) 1 d P C 1 N1A N 0.0252(5) 0.2082(8) 0.5702(3) 0.0296(15) Uiso 0.640(6) 1 d PD C 1 H01A H -0.0410 0.2362 0.5354 0.035 Uiso 0.640(6) 1 calc PRD C 1 C1A C 0.1396(9) 0.3238(15) 0.5771(5) 0.040(3) Uiso 0.640(6) 1 d P C 1 O2 O 0.26758(19) -0.0994(3) 0.47583(13) 0.0418(6) Uani 1 1 d . . . H02 H 0.2044 -0.1750 0.4774 0.063 Uiso 0.35 1 calc PR . . O3 O 0.36518(19) -0.4023(3) 0.53073(13) 0.0427(6) Uani 1 1 d . . . H03 H 0.2915 -0.4457 0.5265 0.064 Uiso 0.65 1 calc PR . . C10 C 0.3654(3) -0.2070(4) 0.50365(15) 0.0295(7) Uani 1 1 d . . . C11 C 0.4923(3) -0.1055(4) 0.50724(16) 0.0325(7) Uani 1 1 d . . . H11A H 0.5408 -0.1333 0.5584 0.039 Uiso 1 1 calc R . . H11B H 0.5334 -0.1894 0.4724 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0492(19) 0.0355(16) 0.0387(18) 0.0095(14) 0.0035(15) -0.0107(14) C3 0.0385(16) 0.0218(14) 0.0313(16) 0.0014(11) 0.0089(12) -0.0021(12) C4 0.0371(16) 0.0349(16) 0.0356(17) 0.0033(12) 0.0134(14) 0.0017(12) C5 0.066(2) 0.0226(15) 0.053(2) 0.0031(14) 0.0126(18) 0.0040(14) C6 0.051(2) 0.0350(17) 0.094(3) 0.0194(19) 0.004(2) 0.0156(15) C7 0.055(2) 0.081(3) 0.046(2) 0.022(2) -0.0122(17) -0.014(2) C8 0.063(2) 0.060(2) 0.039(2) -0.0088(16) 0.0080(18) -0.0133(18) C9 0.0433(17) 0.0369(16) 0.0377(17) -0.0038(13) 0.0162(14) -0.0026(13) O1 0.033(3) 0.039(3) 0.054(4) 0.022(3) -0.004(3) -0.010(2) O1A 0.043(2) 0.046(2) 0.057(2) 0.0271(17) 0.0132(17) -0.0067(15) O2 0.0380(12) 0.0346(12) 0.0494(14) 0.0018(10) -0.0001(10) 0.0003(9) O3 0.0410(12) 0.0348(12) 0.0536(14) 0.0128(10) 0.0126(10) -0.0039(9) C10 0.0376(16) 0.0278(15) 0.0245(15) -0.0033(12) 0.0094(12) -0.0026(13) C11 0.0413(16) 0.0319(14) 0.0258(15) -0.0036(12) 0.0107(13) -0.0011(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N1A 1.453(6) . ? C2 C1 1.519(12) . ? C2 C3 1.536(4) . ? C3 C9 1.517(4) . ? C3 C5 1.525(4) . ? C3 C4 1.545(4) . ? C4 C1A 1.438(10) . ? C4 N1 1.515(11) . ? C5 C6 1.524(5) . ? C6 C7 1.518(6) . ? C7 C8 1.510(5) . ? C8 C9 1.523(4) . ? O1 C1 1.162(13) . ? C1 N1 1.373(16) . ? O1A C1A 1.217(10) . ? N1A C1A 1.393(10) . ? O2 C10 1.247(3) . ? O3 C10 1.269(3) . ? C10 C11 1.479(4) . ? C11 C11 1.311(5) 3_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1A C2 C1 13.1(5) . . ? N1A C2 C3 104.4(3) . . ? C1 C2 C3 106.0(5) . . ? C9 C3 C5 109.8(2) . . ? C9 C3 C2 109.9(2) . . ? C5 C3 C2 111.8(2) . . ? C9 C3 C4 110.3(2) . . ? C5 C3 C4 111.8(2) . . ? C2 C3 C4 103.1(2) . . ? C1A C4 N1 8.8(6) . . ? C1A C4 C3 106.7(4) . . ? N1 C4 C3 103.3(4) . . ? C6 C5 C3 111.9(2) . . ? C7 C6 C5 111.1(3) . . ? C8 C7 C6 111.1(3) . . ? C7 C8 C9 110.5(3) . . ? C3 C9 C8 113.7(2) . . ? O1 C1 N1 112.4(10) . . ? O1 C1 C2 128.5(9) . . ? N1 C1 C2 103.3(9) . . ? C1 N1 C4 113.7(9) . . ? C1A N1A C2 113.2(5) . . ? O1A C1A N1A 115.4(7) . . ? O1A C1A C4 132.4(7) . . ? N1A C1A C4 107.5(7) . . ? O2 C10 O3 124.5(2) . . ? O2 C10 C11 119.7(2) . . ? O3 C10 C11 115.8(2) . . ? C11 C11 C10 122.8(3) 3_656 . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.64 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.488 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.056